ethyl 2-(5-methoxy-4-oxo-3,4-dihydro-2H-chromen-2-yl)acetate | 1222172-63-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: ethyl 2-(5-methoxy-4-oxo-3,4-dihydro-2H-chromen-2-yl)acetate
• 英文别名: ethyl 2-(5-methoxy-4-oxochroman-2-yl)acetate；Ethyl 2-(5-methoxy-4-oxo-2,3-dihydrochromen-2-yl)acetate；ethyl 2-(5-methoxy-4-oxo-2,3-dihydrochromen-2-yl)acetate
• CAS: 1222172-63-5
• 化学式: C₁₄H₁₆O₅
• 分子量: 264.278
• InChiKey: OGPOVFBCDAKMOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-(2-羟基-6-甲氧基苯基)乙基-1-酮 在 三氟甲磺酸三甲基硅酯 、 sodium hydride 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 生成 ethyl 2-(5-methoxy-4-oxo-3,4-dihydro-2H-chromen-2-yl)acetate
  参考文献：
  名称：

  Access to 2-alkyl chromanones via a conjugate addition approach

  摘要：

  The introduction of alkyl substituents at C-2 of chromanones via conjugate addition of silyl enol ethers to a variety of chromenones is reported. In most cases racemic 2-alkyl chromanones were obtained in good yield in the presence of TMSOTf. The copper(II)-promoted conjugate addition of silyl enol ethers to chromenones was also carried out, albeit in low yields and no selectivity. Reliable syntheses of the chromenones via acylation of the corresponding beta-diketo-compounds are also described. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.05.115

文献信息

• One-pot reaction of ortho-acylphenols and terminal alkynoates for synthesis of 2-alkyl-substituted chromanones
  作者：Ling-Guo Meng、Hui-Fang Liu、Jian-Long Wei、Sun-Na Gong、Song Xue

  DOI：10.1016/j.tetlet.2010.01.093

  日期：2010.3

  A facile synthesis of 2-alkyl-substituted chromanones from ortho-acylphenols and terminal alkynoates is described. The method contains two consecutive processes in one-pot reaction through a DABCO-catalyzed condensation reaction and a KOBu'-mediated intramolecular cycloaddition to afford the desired products. (C) 2010 Elsevier Ltd. All Fights reserved.
• Access to 2-alkyl chromanones via a conjugate addition approach
  作者：Louise A. Stubbing、Freda F. Li、Daniel P. Furkert、Vittorio E. Caprio、Margaret A. Brimble

  DOI：10.1016/j.tet.2012.05.115

  日期：2012.8

  The introduction of alkyl substituents at C-2 of chromanones via conjugate addition of silyl enol ethers to a variety of chromenones is reported. In most cases racemic 2-alkyl chromanones were obtained in good yield in the presence of TMSOTf. The copper(II)-promoted conjugate addition of silyl enol ethers to chromenones was also carried out, albeit in low yields and no selectivity. Reliable syntheses of the chromenones via acylation of the corresponding beta-diketo-compounds are also described. (C) 2012 Elsevier Ltd. All rights reserved.